The present invention relates to a novel compound, 3-hydroxypropyl ester of 2-trifluoromethylacrylic acid, represented by the after-mentioned formula [1], and its production process. This 3-hydroxypropyl ester can also be named 3-hydroxypropyl 2-(trifluoromethyl)acrylate.
Fluorine-containing compounds have been used or developed in various fields particularly in the field of advanced materials due to their good qualities (e.g., water repellency, oil repellency, low water absorption, heat resistance, weather resistance, corrosion resistance, transparency, photosensitivity, low refractive index, and low dielectric property). In particular, they are used in the coating field in view of their characteristic transparency behavior in each wavelength. Recently, there have been active researches and developments of (a) anti-reflection films taking advantage of their low refractive indexes and visible light transparency, (b) optical devices taking advantage of their transparency in long wavelength band (optical communication wavelength band), and (c) resist compositions taking advantage of their transparency in ultraviolet region (particularly vacuum ultraviolet region).
A common aim in polymer design of such researches and developments is to achieve good adhesion to substrate and high glass transition point (hardness), while achieving transparency in each wavelength for use by introducing as many fluorine atoms as possible. There are various proposals of increasing transparency at each wavelength by increasing the fluorine content in material design. However, there are few reports on improving fluorine-containing monomers themselves in hydrophilicity and adhesion and on obtaining high glass transition point.
Acrylic and methacrylic esters have an ethylenic unsaturated bond in the molecule and are widely used as raw materials for producing polymers, in various fields such as paint, adhesive, ink, resist material and paper-processing agent (see Japanese Patent Laid-open Publication JP-A-3-41051). Acrylic and methacrylic esters containing a hydroxyl group in the ester chain exhibit a good hydrophilicity. Therefore, they are used as a raw material for producing contact lens and anti-fogging lens plastics. Furthermore, they have recently been used as a dripping inhibitor of flame-retardant pressure sensitive adhesive tapes (see JP-A-2004-083730).
Fluorinated acrylic and methacrylic esters are used mainly in the fields of photochemistry and radiation chemistry (see JP-A-57-104906 and JP-A-58-018608). Polyacrylate and polymethacrylate, which contain a trifluoromethyl group in an acyl moiety in the molecule, have a less degree of cross-linking, as compared with non-fluorinated compounds, and thus used as a positive resist material. (see T. G. Tessier, et al., Polymer Engineering & Science, pp. 1,000 (1983)).
Hitherto, there have not been sufficient examinations as to whether or not acrylic and methacrylic esters, which have a trifluoromethyl group in the acyl moiety of their molecule and a hydroxyl group at the end of the ester chain, are effective as functional materials. As a compound having a trifluoromethyl group in the acyl moiety of the molecule and a hydroxyl group at the end of the ester chain, there is known 2-hydroxyethyl ester of 2-trifluoromethylacrylic acid (2-hydroxyethyl 2-(trifluoromethyl)acrylate) represented by the formula [4] (Registry Number: 450358-94-8 in Chemical Abstracts Service (CAS)).
However, the production process and the use of this compound have not been reported.